Antiallergy and antiinflammatory agents, compositions and use

• US 5,036,088 A
• Filed: 12/03/1990
• Issued: 07/30/1991
• Est. Priority Date: 06/09/1986
• Status: Expired due to Fees

• Current Assignee: Pfizer Inc.
• Original Assignee: Pfizer Inc.
• Inventors: Asai, Nobuko, Kitaura, Yoshihiko, Ito, Fumitaka, Stevens, Rodney W.
• Primary Examiner(s): Lee, Mary C.
• Assistant Examiner(s): NOT, DEFINED
• Application Number:
  US07/620,959
• Time in Patent Office: 239 Days
• Field of Search: 548/221, 548/305, 546/270, 546/271, 514/338, 514/375, 514/387
• US Class Current: 514/375
• CPC Class Codes: C07D 209/34 in position 2
• CPC Class Codes: C07D 209/38 in positions 2 and 3, e.g. isatin
• CPC Class Codes: C07D 235/26 Oxygen atoms
• CPC Class Codes: C07D 263/58 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
• CPC Class Codes: C07D 277/68 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
• CPC Class Codes: C07D 413/12 linked by a chain containing hetero atoms as chain links

Abstract

Compounds of the formula ##STR1## where Y is alkyl, aryl or heterocyclic, n is 1-7, R is hydrogen, alkyl, aralkyl or carboxymethyl, R₁ is acetoxy, thiophenoxy, hydrogen, halo, alkyl, alkoxy or trifluoromethyl, R₂ is hydrogen, alkyl or alkanoyl and X is C═O, CH₂, NH, O or S as antiallergy and antiinflammatory agents.

Claims

1. A compound of the formula ##STR56## or a pharmaceutically acceptable acid addition salt thereof, wherein R is hydrogen, alkyl having one to three carbon atoms, benzyl or carboxymethyl;

R₁ is acetoxy, thiophenoxy, hydrogen, fluoro, chloro, methoxy, methyl or trifluoromethyl;

R₂ is hydrogen, alkyl having one to three carbon atoms, alkanoyl having one to three carbon atoms or benzyl;

X is NH, or O;

n is an integer of 1 to 7; and

Y is styryl, methyl, N-methylphenylamino, N-benzylphenylamino, phenylamino, phenoxy, thiophenoxy, thienyl, furyl, pyridyl, phenyl, substituted phenyl wherein said substituent is methyl, dimethylamino, methoxy, fluoro or chloro, or disubstituted phenyl wherein said substituents are each chloro, hydroxy or methoxy with the proviso that when Y is phenoxy, thiophenoxy, phenylamino, N-methylphenylamino or N-benzylphenylamino n is 2-7.

2. A compound of claim 1, wherein X is NH, R is alkyl having one to three carbon atoms, R₁ is alkoxy having from one to three carbon atoms and R₂ is hydrogen.

3. A compound of claim 2, wherein n is 1 and Y is styryl.

4. A compound of claim 2, wherein n is 3 and Y is phenyl.

5. A compound of claim 2, wherein n is 1 and Y is phenyl.

6. A compound of claim 2, wherein n is 2 and Y is styryl.

7. A compound of claim 1, wherein X is O, Y is pyridyl, styryl, methyl, phenyl, thienyl or substituted phenyl wherein said substituent is methyl, dimethylamino, methoxy, fluoro or chloro;

R is hydrogen or alkyl having one to three carbon atoms;

R₁ is hydrogen, acetoxy, thiophenoxy, fluoro, chloro, methoxy or methyl; and

R₂ is hydrogen or alkyl having one to three carbon atoms.

8. A compound of claim 7, wherein Y is methyl or phenyl, R and R₁ are each hydrogen and n is 1, 3 or 5.

9. A compound of claim 7, wherein Y is phenyl or pyridyl, R and R₂ are each hydrogen, n is 1, 3 or 5 and R₁ is methyl, methoxy, fluoro or chloro substituted at the 5-position.

10. A pharmaceutical composition for the treatment of allergic or inflammatory conditions in a mammal, said composition comprising an effective amount of a compound according to claim 1, with a pharmaceutically acceptable carrier.

11. A method for treating an allergic or inflammatory condition in a mammal which comprises administering to said mammal an antiallergy or anti-inflammatory effective amount of a compound according to claim 1.